Synthetic investigations in the sesamin group - Part I. Synthesis of samin, a degradation product of sesamolin

Banerjee, DK and Bhute, RS and Murty, NLN (1963) Synthetic investigations in the sesamin group - Part I. Synthesis of samin, a degradation product of sesamolin. In: Proceedings of the Indian Academy of Sciences - Section A, 58 (3). pp. 153-160.

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Abstract

Ethylα-bromovinylacetate (VII) was condensed with the sodio derivative of ethyl piperonoylacetate (VIII) to give diethylα-vinyl-α′-piperonoylsuccinate (IX). The latter on reduction with lithium aluminium hydride furnished the triol (X), which underwent smooth cyclisation with 1% ethanolic hydrogen chloride to 2-(3′, -methylenedioxyphenyl)-hydroxymethyl-4-vinyltetrahydrofuran (XIa). The structure of XIa was established by Oppenauer oxidation to an aldehyde. Ozonolysis of XIa afforded samin (I).

Item Type:	Journal Article
Publication:	Proceedings of the Indian Academy of Sciences - Section A
Publisher:	Indian Academy of Sciences
Additional Information:	Copyright of this article belongs to Indian Academy of Sciences.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	03 Jun 2010 04:34
Last Modified:	19 Sep 2010 06:08
URI:	http://eprints.iisc.ac.in/id/eprint/28198

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